HCID 69334832, compound → HCID 54495358, compound

HRID 1003192Notes

Reaction equation

HRID 1003192 reaction equation
C([O:8][C:9]1[C:26]([N:27]([CH3:29])[CH3:28])=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C:18](=[O:30])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)C1C=CC=CC=1>C1COCC1.[Pd]>[CH3:29][N:27]([CH3:28])[C:26]1[C:9]([OH:8])=[CH:10][C:11]2[CH2:12][CH2:13][C@@H:14]3[C@@H:23]([C:24]=2[CH:25]=1)[CH2:22][CH2:21][C@@:19]1([CH3:20])[C@H:15]3[CH2:16][CH2:17][C:18]1=[O:30]

Participants

4

Reactant 1

HCID 69334832HCID 69334832, compound

Product 1

HCID 54495358HCID 54495358, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-benzyloxy-2-dimethylaminoestra-1,3,5(10)-trien-17-one (81, 0.666 g, 1.65 mmol) in THF (30 mL) was added 10% palladium on carbon (0.200 g). The reaction mixture was stirred for 1 h under a hydrogen atmosphere at room temperature. After the catalyst was filtered, the solvent was evaporated at reduced pressure. The residue was purified by column chromatography (silica gel) using n-hexane:EtOAc (3:1→2:1, v/v) to afford 0.462 g of 82 (89% yield) mp: 160-161° C.

Workup

  1. filtrationAfter the catalyst was filtered
  2. customthe solvent was evaporated at reduced pressure
  3. customThe residue was purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-24701eec3c5a4d7195648f283e1f0f88
Source dataset
uspto-grants-2000_04
Patent number
US06046186

Reaction notes

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